StyleJonathan Cavaliere

Dressing the Groomsmen: My Menswear Journey as Best Man

StyleJonathan Cavaliere
Dressing the Groomsmen: My Menswear Journey as Best Man

If you follow me on Instagram, you would know that over the course of this year I have been involved with helping prepare one of my closest friends, Matthew Anneccharico, for his wedding.

You may recognize him from a couple of posts on the site, including the Style Upgrade with his beautiful daughter, Sophia, and more recently the Johnnie Walker groomsmen tasting I held for him back in September.

As his best man, I was truly honored when he asked me to join him on his special day. I accepted it as a challenge and like any guy who hasn’t been in this position before, I took to the internet for answers. Whether it was choosing colours with him and his bride or writing a speech that was both funny and sentimental, I had a ton of fun along the way.

As the menswear enthusiast of the group, I was also assigned to dress both Matt and his 11 groomsmen. Being such a large group with varying body shapes, I knew I had to find a brand that would not only be stylish, but also draped well on each of the guys. Before long, I thought of one of my long-time partners and dear friends at RW&CO. The selection there is not only vast, but very cost efficient.As the bridesmaids were wearing aubergine-coloured gowns, I knew that our ties and suits had to compliment them. After various trips to RW&CO.’s Yorkdale and Eaton’s Centre locations, we finally made our decision.

I decided on a heather grey two-piece suit with a contrasting glen check vest. For the shirts, we went with a clean white cuff link shirt and accessorized them with aubergine-coloured bowties and burgundy polka dotted pocket squares.

As for Matt, I wanted to go classic and sophisticated. For this reason, I gifted him in a black peaked lapelled tuxedo, a while tuxedo shirt with black buttons, a black silk bow tie, a clean white pocket square, and black patent lace ups. The look on Matt’s face when I put it all together at the hotel room the night before is one I will never forget.


I want to thank RW&CO. for being so helpful over the months leading up to the wedding and taking some of the stress away from planning the big day. To see their full suiting collection head over to

Words by Jonathan Cavaliere